section 10 ² substitution reactions (sn1, sn2… · section 10 ² substitution reactions (sn1,...
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SECTION 10 SUBSTITUTION REACTIONS (SN1, SN2) AND
ELIMINATION REACTIONS (E1, E2)
10-1 -- Overview of Nucleophilic Substitutions and Eliminations
SN2 Reaction
SN1 Reaction
E2 Reaction
E1 Reaction
10-1 -- The SN2 Reaction
Bimolecular, Nucleophilic, Substitution
Stereochemistry
Back-side Displacement and Inversion of Absolute Configuration
Effect of Alkyl Halide Structure (1°, 2°, 3°)
Branching at the Beta-Carbon ( -Carbon)
Nucleophilicity and its Dependence on the Solvent
Steric Bulk Considerations
Leaving Groups (l.g s)
The Tosylate Leaving Group (-OTs, or p-toluenesulfonate)
Intramolecular SN2 Reactions
10-9 -- The E2 Reaction
Bimolecular Elimination; Beta-Elimination ( -Elimination)
Stereochemistry
C-H and C-X = Periplanar
Syn-Periplanar vs. Anti-Periplanar
Regiochemistry Concerns
Multiple -H s
Zaitsev s Rule
Small Bases vs. Large Bulky Bases
Cyclic Systems (Rings) and the E2 Reaction
The E2 Reaction and Cyclohexane Chair Conformations
10-14 -- Competition Between SN2 and E2 Reactions
3° Halides, 2° Halides, and 1° Halides
10-15 -- E2 Elimination of Vinyl Halides
Converting Alkenes to Alkynes
10-16 -- SN1 and E1 Reactions
Unimolecular (First-Order)
Ionization of the Alkyl Halide (R-X)
The Rate-Determining Step ( Rate-Limiting Step )
Solvolysis
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Ionization Step in Detail
Best Leaving Groups
Formation of Allylic and Benzylic Carbocations
Alkyl Substitution and Carbocation Stability
Solvent Effects on the SN1 / E1 Ionization Step
Polar or Non-Polar Solvents?
The Dielectric Constant ( )
Product Determining Step(s)
Carbocations
SN1 Stereochemistry
E1 Regiochemistry and Zaitsev s Rule
10-21 -- SN2 vs. E2 vs. SN1/E1
When are SN2 and E2 Favored?
Is There a Good Leaving Group (l.g)?
Is There a Good Nucleophile Present?
When are SN1 and E1 Favored?
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SECTION 10 – SUBSTITUTION REACTIONS (SN2, SN1) AND ELIMINATION REACTIONS (E2, E1)
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